CN100360619C - Process for preparing carbon products having organic group linked to carbon material - Google Patents

Process for preparing carbon products having organic group linked to carbon material Download PDF

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CN100360619C
CN100360619C CNB011046538A CN01104653A CN100360619C CN 100360619 C CN100360619 C CN 100360619C CN B011046538 A CNB011046538 A CN B011046538A CN 01104653 A CN01104653 A CN 01104653A CN 100360619 C CN100360619 C CN 100360619C
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carbon
diazonium salt
group
acid
primary amine
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CN1319627A (en
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詹姆斯·A·贝尔蒙特
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Cabot Corp
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Cabot Corp
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    • C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
    • C04B35/622—Forming processes; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
    • C04B35/626—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B
    • C04B35/63—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B using additives specially adapted for forming the products, e.g.. binder binders
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    • C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
    • C04B35/515—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on non-oxide ceramics
    • C04B35/52—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on non-oxide ceramics based on carbon, e.g. graphite
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    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
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    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/44—Carbon
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    • C09C1/56—Treatment of carbon black ; Purification
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    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/44—Carbon
    • C09C1/48—Carbon black
    • C09C1/56—Treatment of carbon black ; Purification
    • C09C1/565—Treatment of carbon black ; Purification comprising an oxidative treatment with oxygen, ozone or oxygenated compounds, e.g. when such treatment occurs in a region of the furnace next to the carbon black generating reaction zone
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    • C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
    • C09C3/08—Treatment with low-molecular-weight non-polymer organic compounds
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    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
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    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
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    • C09D5/02—Emulsion paints including aerosols
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    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/41—Organic pigments; Organic dyes
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F11/00—Chemical after-treatment of artificial filaments or the like during manufacture
    • D01F11/10—Chemical after-treatment of artificial filaments or the like during manufacture of carbon
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    • C04B2235/00—Aspects relating to ceramic starting mixtures or sintered ceramic products
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  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
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Abstract

Processes for preparing a carbon product having an organic group attached to a carbon material. The carbon material is selected from graphite powder, a graphite fiber, a carbon fiber, a carbon cloth, a vitreous carbon product, and an activated carbon product. In one process at least one diazonium salt reacts with a carbon material in the absence of an externally applied electric current sufficient to reduce the diazonium salt. In another process at least one diazonium salt reacts with a carbon material in a protic reaction medium.

Description

Preparation has the method for the carbon products of linking the organic group on the carbon material
The present invention be submitted on December 15th, 1994, application number is 95197591.9, exercise question is divided an application for " preparation has the method for the carbon products of the organic group to the carbon material ".
The present invention relates to the preparation method of carbon products.This method relates to diazonium salt and carbon material reaction, generates to have the carbon products of linking the organic group on this carbon material.This carbon material is selected from Graphite Powder 99, graphite material, carbon fiber, carbon fabric, vitreous carbon product and activated carbon products.
Carbon material is used for various industry and product.These carbon materials comprise: for example, Graphite Powder 99, graphite fibre, carbon fiber, carbon fabric, vitreous carbon product and activated carbon products, many purposes of these carbon materials are discussed below.
Graphite Powder 99 except it is used as " lead " in pencil, also is used for many fields, comprises electronics, chemistry, metallurgy and rocket element.The electrode of being made by graphite is used for steel melting furnace and electrolytic preparation chlorine, oxymuriate, magnesium and sodium.Graphite also is used for preparing metallurgical mould, crucible and chemical reaction container.In the rocket field, graphite is as rocket electric motor nozzle and guided missile nose cone.
Graphite fibre and carbon fiber are used for various fields similarly.The toughener of short or broken fiber in being commonly used for moulding and braking automobile (these places need good abrasion resistance).High-performance graphite or carbon fiber are used for structural composite material, particularly the matrix material used of those aviation fields.These fibers also are widely used for movement value, as fishing rod, golf club and tennis racket.
Carbon fabric or blanket sheet are the simple fabric by the macrofiber preparation of carbon or graphite.They can be used for following these fields: carpet or relate to the xeroprinting of static dissipative, electromagnetic shielding and plate material forming trolley part in the furniture of computer.This low heat conductivity also can be used for rocket element field.
Vitreous carbon is used for the preparation of electronic product such as electrode and engineering goods (as crucible).
Activated carbon has good adsorptivity, therefore is used for improving the chemical that makes, the color of oil ﹠ fat, control water, the color of drink and food, aroma and flavor.These gas adsorption carbon also are used for recovery, air-conditioning system and the gas shroud of gas delivery operation, solvent vapour.
Made the surface chemistry that many effort change carbon material in the past in decades.When might the Material Physics of having adsorbed when depositing on the carbon material surface, forever change its surface chemistry and be actually more difficult.
PCT patent application WO 92/13983 has introduced a kind of method of being come the carbonaceous material surface is carried out modification by the diazonium salt electrochemical reduction.It is reported that this method can be used for, particularly the carbon plate of matrix material and carbon fiber.Also introduced carbonaceous material by this method modification.People such as Delmar " Americanized scholar association " (J.Am.Chem.Soc.) 1992,114,5883-5884 has also introduced the diazonium salt covalent modification carbon surface that electrochemical reduction contains functionalized aryl.
According to WO 92/13983, the method for carbonaceous material surface modification is comprised that the diazonium salt that contains an aromatic group by electrochemical reduction is grafted to this aryl on the surface of this material.This carbonaceous material is contacted with diazonium salt in aprotonic solvent, and make it electronegative with respect to the anode that also contacts with this diazonium salt solution.Report uses protic solvent to make this electrochemical method can not generate desired product, and the result has reduced the diazonium triple bond, has generated hydrazine.
Although technology discussed above is arranged, still need the surface chemistry of modified carbon black and give carbon black needed performance.
Therefore, the present invention relates to prepare the method for the carbon products that contains an organic group, this organic group is linked and is selected from the following carbon material: Graphite Powder 99, graphite fibre, carbon fiber, carbon fabric, vitreous carbon product and activated carbon products.Be connected on this carbon black.Method is included in is not enough to reduce the step of at least one diazonium salt and carbon material reaction under the impressed current condition of this diazonium salt.
The another one method is included at least a diazonium salt and carbon material reaction in the alpha proton reaction medium.
Following specification sheets has been introduced other feature and advantage of the present invention.These effects are more obvious by this specification sheets introduction, or can understand these effects by described enforcement of the present invention.By particularly below in the specification sheets and method, product and the composition pointed out in the appending claims, will understand and realize purpose of the present invention and other advantages.
The method for preparing carbon black products
First embodiment of the present invention provides preparation to contain the method for the carbon products of an organic group, and this organic group is linked on this carbon material.This carbon material is selected from Graphite Powder 99, graphite fibre, carbon fiber, carbon fabric, vitreous carbon product and activated carbon products.
Method is included in is not enough to reduce at least a diazonium salt and carbon material reaction under the impressed current of diazonium salt.That is be not to be enough to reduce carry out under the condition of the external electric component of this diazonium salt, in the reaction between diazonium salt and the carbon material.The mixture of different diazonium salts can be used in this method of the present invention.Can in reaction medium, (comprise proton and aprotonic solvent system or slurry) and carry out this method under the various reaction conditionss, at any kind.
In another method, at least a diazonium salt and carbon material reaction in the alpha proton reaction medium.Can in this method of the present invention, use the mixture of different diazonium salts.Also can under various reaction conditionss, carry out this method.
Preferably, in two methods, on-the-spot this diazonium salt that forms.If necessary, in any one method, available methods known in the art are separated and in dry this carbon products.In addition, the available already known processes carbon products of handling this generation is removed impurity.The preferred embodiment of these methods is discussed below and in embodiment.
The carbon material that is used for the inventive method is the carbon material that is selected from Graphite Powder 99, graphite fibre, carbon fiber, carbon fabric, vitreous carbon product and activated carbon products.The carbon black products of this generation can be used in the known application of untreatment carbon material.The more important thing is that available method of the present invention prepares the carbon products of the unexistent premium properties of untreatment carbon material.
Can carry out the method for this invention under various conditions, and be not limited to any concrete condition usually.It can't be otherwise for reaction conditions, makes this concrete diazonium salt enough stable to allow it and carbon material react.Therefore, can be to carry out these methods under the reaction conditions that exists the short period of time at diazonium salt.Reaction between diazonium salt and the carbon material is for example carried out in very wide pH scope and temperature range.Can under acidity, neutrality and alkaline pH, carry out these methods.Preferred this pH changes between about 1-9.This temperature of reaction is preferably in 0 ℃ of-100 ℃ of scope.Diazonium salt as known in the art can prepare by the reaction of for example primary amine and nitrous acid aqueous solution." organic chemistry " (Organic Chemistry) of Morrison and Boyd seen in the generality discussion of diazonium salt and its preparation method, the 5th edition, the 937-983 page or leaf, (Allyn andBacon, Inc.1987) and " Advanced Organic Chemistry: reaction, mechanism and structure " (AdvancedOrganic Chemistry:Reactions of March, Mechanisms and Structures), the 4th edition, (Wiley, 1992).According to the present invention, diazonium salt is the organic compound with one or more diazonium groups.
In the method for the invention, this diazonium salt can make before reacting with carbon material, or more preferably used the already known processes scene of this area to make." scene " preparation also allows to use unsettled diazonium salt such as alkyl diazonium salt, and has avoided this diazonium salt is carried out unnecessary processing or operation.In the particularly preferred method of the present invention, two of nitrous acid and diazonium salts all are on-site preparations.
Diazonium salt as known in the art can prepare by primary amine, nitrite and acid-respons.This nitrite can be any nitrous acid metal-salt, and preferably lithium nitrite, inferior sodium nitrate, potassium nitrite or zinc nitrite, or any organic nitrous acid ester are as Isopentyl nitrite or ethyl nitrite.This acid can be effectively any inorganic or organic acid in generating this diazonium salt.Preferred acid comprises nitric acid HNO 3, spirit of salt HCl and sulfuric acid H 2SO 4
This diazonium salt also can prepare by primary amine and nitrogen peroxide reactant aqueous solution.The aqueous solution NO of this nitrogen peroxide 2/ H 2O provides to generate the required nitrous acid of this diazonium salt.
Generating diazonium salt in the presence of excessive HCl is not too preferred than additive method, because HCl is to Corrosion of Stainless Steel.Use NO 2/ H 2O generates diazonium salt and has stainless steel or the less attendant advantages of other metal protections to being generally used for reaction vessel.Use H 2SO 4/ NaNO 2Or HNO 3/ NaNO 2The corrodibility of preparation is also smaller relatively.
In general, generating diazonium salt from primary amine, nitrite and acid need be based on the two normal acid of used amine.In " scene " method, available monovalent acid generates this diazonium salt.When this primary amine contains a strong acid, need not add other acid in the method for the invention.The Equivalent that an acidic group of primary amine or a plurality of acidic group can provide one or two required acid.When this primary amine contains a strong acid group, preferably do not add other sour or adding and be up to normal other acid to method of the present invention, come on-the-spot this diazonium salt that generates.Can use other excessive slightly acid.An example of this primary amine is right-aniline sulfonic acid (sulfanilic acid).
Usually, diazonium salt is heat-labile.That they normally prepare in low temperature (as 0-5 ℃) solution and under the unseparated situation of salt, use.The solution that heats some diazonium salts can be emitted nitrogen and be formed corresponding alcohol or form organic free radical in acidic medium in alkaline medium.
Yet in order to implement method of the present invention, this diazonium salt only needs enough to stablize with carbon material to react just.Therefore, method of the present invention can be thought instability and the diazonium salt that is easy to decompose carries out in other cases with some.Some decomposition coursees can and this carbon material and diazonium salt between response competition, and can reduce the sum that is connected to the organic group on this carbon material.In addition, this reaction can be carried out under higher temperature, and at this moment many diazonium salts are easy to decompose.Higher temperature also can advantageously increase the solvability of this diazonium salt in reaction medium and the processibility of raising in its this method.Yet because other decomposition course, higher temperature can cause the loss of some diazonium salts.
The inventive method can be implemented by add the on-the-spot diazonium salt that forms of reagent in the mixture of the carbon material in reaction medium (as water) or suspension.Therefore, mixture to be used in the method for the invention or suspension can comprise that one or more reagents form diazonium salt, and just can implement method of the present invention by adding remaining reagent.
Common a large amount of functional groups are suitable for forming the reaction of diazonium salt in organic compound.Therefore, only there is the availability of the diazonium salt that reacts with carbon material to limit method of the present invention.
Carry out in the reaction medium that method of the present invention can be reacted between any permission diazonium salt and carbon material.Preferably, this reaction medium is based on the system of solvent.This solvent can be the mixture of protic solvent, aprotonic solvent or solvent.Protic solvent is as water or methanol solvent, contains the hydrogen atom that is connected to Sauerstoffatom or nitrogen-atoms, and therefore has enough acidity to form hydrogen bond.Aprotonic solvent is the solvent that does not contain acid hydrogen atom.Aprotonic solvent comprises: for example, and as the solvent of hexane, tetrahydrofuran (THF) (THF), acetonitrile and benzonitrile.To the discussion of proton and aprotic solvent, referring to " organic chemistry " (Organic Chemistry) of Morrison and Boyd, the 5th edition, the 228-231 page or leaf (Allyn and Bacon, Inc.1987).
Method of the present invention is preferably carried out in a kind of protic reaction medium, promptly in independent a kind of protic solvent or contain in the solvent mixture of at least a protic solvent and carry out.Preferred proton medium includes, but are not limited to: water, the aqueous medium that contains water and other solvents, alcohol and contain any medium of alcohol or the mixture of these media.
In general, method of the present invention has produced inorganic byproduct, as salt.In some target purposes, as those purposes of discussing below, these by products may be undesirable and be debatable.The method according to this invention, some prepare carbon products and do not have the feasible method of undesired inorganic byproduct or salt as follows:
At first, remove before use with any means known in this area and not wish the inorganic byproduct wanted, come this diazonium salt of purifying.The second, with the diazo reagent of organic sub-nitrate, rather than use inorganic salt as the generation correspondent alcohol, generate this diazonium salt.The 3rd, as amine and water-based NO from having acidic group 2When generating diazonium salt, do not form inorganic salt.Some other method is known those skilled in the art.
Except generating inorganic byproduct, method of the present invention also can produce organic by-products.These organic by-products can be by removing with organic solvent extraction.Additive method is known for those skilled in the art.
Carbon products
Diazonium salt and the reaction between the carbon material in the inventive method have formed the carbon products with an organic group, and this organic group is connected on the carbon material that is selected from Graphite Powder 99, graphite fibre, carbon fiber, carbon fabric, vitreous carbon product and activated carbon products.This diazonium salt can contain the organic group that is connected on the carbon black.This organic group can be aliphatic group, ring-type organic radical or have the organic compound of aliphatic series part and circular part.As mentioned above, employed diazonium salt can prepare from a kind of like this primary amine in the inventive method, and this primary amine has such group and can form (even astable form), a kind of diazonium salt.This organic radical can be replace or non-replacement, branching or non-branching.Aliphatic group comprises: for example, and from alkane, alkene, alcohols, ethers, aldehydes, ketone, carboxylic-acid and carbohydrate deutero-base.Cyclic organic group includes, but are not limited to: alicyclic hydrocarbon radical (as cycloalkyl, cycloalkenyl group), heterocycle alkyl (as pyrrolidyl, pyrrolinyl, piperidyl, morpholinyl etc.), aryl (as phenyl, naphthyl, anthryl etc.) and heteroaryl (as imidazolyl, pyrazolyl, pyridyl, thienyl, thiazolyl, furyl, indyl etc.).When sterically hindered increases of the organic group that replaces, react the number that is connected to the organic group on this carbon material from this diazonium salt and carbon material and may reduce.
When this organic group was substituted, it can contain any functional group that diazonium salt forms that is suitable for.Preferred functional group includes, but are not limited to: OR, COR, COOR, OCOR, COONa, COOK, COO -NR 4 +, halogen, CN, NR 2, S n, SO 3H, SO 3Na, SO 3K, SO 3 -NR 4 +, NR (COR), CONR 2, NO 2, PO 3H 2, PO 3HNa, PO 3Na 2, N=NR, NR 3 +X -And PR 3 +X -R is hydrogen atom, C independently 1-C 20Alkyl (branching or nonbranched) or aryl.Integer n changes in 1-8, and preferably changes between 2-4.Negatively charged ion X -Be halogenide or from mineral acid or organic acid deutero-negatively charged ion.
Preferred organic group is formula A yThe aromatic group of Ar-, it is equivalent to formula A yArNH 2Primary amine.In the formula, the meaning of variable is as follows: Ar is an aromatic group, is selected from phenyl, naphthyl, anthryl, phenanthryl, phenylbenzene, pyridyl; A is the substituting group on the aromatic group, independently is selected from above-mentioned preferred functional group, or A is linearity, branching or cyclic alkyl (preferably containing up to 1-20 carbon atom), does not replace or replace with one or more those functional groups; And when Ar was phenyl, y was the integer of 1-5, and when Ar was naphthyl, y was the integer of 1-7, and when Ar is anthryl, when phenanthryl or phenylbenzene, y is the integer of 1-9, or when Ar was pyridyl, y was the integer of 1-4.
Other one group of organic group that can be connected on this carbon material is an organic group that ion or ionogen replaced that is used as functional group.Ionogen can form ionic group at employed medium.This ionic group can be anionic group or cation group, and this ionizable group can form negatively charged ion or positively charged ion.
Forming anionic ionizable functional group comprises: for example, and the salt of acidic group or acidic group.Therefore, this organic group comprises from organic acid deutero-group.Preferably when it contains the anionic ionogen of formation, an organic group like this has a) aromatic group, and b) at least one has pKa less than 11 acidic group, or at least one has the salt of pKa less than 11 acidic group, or at least one has pKa and has the mixture of pKa less than the salt of 11 acidic group less than 11 acidic group and at least one.The pKa of this acidic group is meant the pKa of whole organic group, and just this acidic group is not substituent.More preferably, this pKa is less than 10, and most preferably less than 9.The aromatic group of preferred this organic group is directly linked on this carbon black.This aromatic group can further be substituted or not replace, as uses alkyl.More preferably, this organic group is a phenyl or naphthyl, and this acidic group is sulfonic group, sulfino, phosphonate group or carboxylic acid group.The example introduction of these acidic groups and their salt as above.Most preferably, this organic group be replace or unsubstituted sulfophenyl or its salt; That replace or unsubstituted (many sulfo groups) phenyl or its salt; That replace or unsubstituted sulphur naphthyl or its salt; That replace or unsubstituted (many sulfo groups) naphthyl or its salt.The preferred sulfophenyl that replaces is hydroxyl sulfophenyl or its salt.
The organic group of the concrete ionizable functional group with formation negatively charged ion (with the corresponding primary amines of using in the methods of the invention) is: right-sulfophenyl (right-sulfanilic acid), 4-hydroxyl-3-sulfophenyl (2-hydroxyl-5-amino-Phenylsulfonic acid) and 2-sulfoethyl (2-aminoethyl sulfonic acid).
Amine represents to form the example of the ionizable functional group of cation group.For example, amine can protonated formation ammonium in acidic medium.Preferably, has the pKb of the substituent organic group of amido less than 5.Quaternary ammonium group (NR 3 +) and quaternary phosphonium  base (PR 3 +) also represent the example of cation group.Preferably, this organic group contains aryl and a quaternary ammonium group or the quaternary phosphonium  base as phenyl or naphthyl.This aryl is preferably directly linked on the carbon black.Season cyclic amine in addition season aromatic amine, also can be used as this organic group.Therefore, the pyridine  compound that N-replaces as N-methyl-pyridyl, can be used on this respect.
An advantage with the carbon material that is connected with organic group that replaces with ion or ionogen is: with respect to corresponding untreatment carbon material, this carbon products can improve water dispersible.Except its water dispersible, have by the carbon products of the organic group of ion or ionogen replacement, also can be dispersed in the polar organic solvent, in dimethyl sulfoxide (DMSO) (DMSO) and methane amide.
The water dispersible of carbon products increases along with the increase that is connected to the number that has the organic group on the ionogen on the carbon material, or increases along with the increase that is connected to the number of specifying the ionogen on the organic group.Therefore, increase the number of linking the ionogen on this carbon products and should improve its water dispersible.Should note:, also can improve and contain amine as the water dispersible that is connected to the carbon products of the organic group on this carbon material by the acidifying aqueous medium.Because the water dispersible of this carbon products depends on the stability of electric charge to a certain extent, thus preferably the ionic strength of this aqueous medium less than 0.1 volumetric molar concentration.More preferably, this ionic strength is less than 0.01 volumetric molar concentration.
When by a kind of like this water dispersible carbon products of method of the present invention preparation, preferably at this this ion of reaction medium intermediate ionization or ionizable group.In addition, this carbon products can carry out drying with the used technology of conventional carbon material.Yet, the over-drying loss that causes the water dispersible degree.
Aromatics sulfide is other one group of preferred organic group.Carbon products with aromatics sulfide group is suitable for rubber combination especially or other has the composition of reactive ethylenic group.These aromatics sulfide can be by formula ArS nAr ' or ArS n" expression, wherein Ar and Ar ' are arylidene independently, Ar, and " be aryl, k is 1-8 to Ar.Preferred arylidene comprises phenylene, and is particularly right-phenylene.Preferred aryl groups comprises phenyl and naphthyl.The number of sulfur atoms that exists is represented by n, preferably in the 2-4 scope.Particularly preferred aromatics sulfo-thing group is two-right-(C 6H 4)-S 2-(C 6H 4)-and right-(C 6H 4)-S 2-(C 6H 5).The diazonium salt of these aromatics sulfide groups can be from its corresponding primary amines H 2N-Ar-S n-Ar '-NF 2Or H 2N-Ar-S x-Ar " conventional preparation.
The purposes of carbon products
Carbon products of the present invention can be used for and the corresponding identical purposes of untreatment carbon material.Yet, link the performance that organic group on this carbon material can be used to change and improve the given carbon material that is used for special purpose.Also can select organic group to link and specify on the used base material of carbon material.This connection can be taked to carry out this method such as sulfuration, neutralization, cooperation or polymerization by the form of a kind of like this method and substrate reaction.An example is to have NH 2The carbon material of base is used for the material based on Resins, epoxy.
Following embodiment is used for explanation, but does not limit the present invention.
Use S.J.Gregg, K.S.W Sing measures surface-area and pore space in " absorption, surface-area and porosity " (Absorption, SurfaceArea and Porosity) (academic press, 1982) described method.Measure surface-area, non-pore surface area and the pore space of activated carbon according to the described method of 90-97.Measure the surface-area of carbon fabric with stepped thermoisopleth according to the described method of 84-86 page or leaf.Measure the surface-area of graphite fibre with krypton by the BET method.
Embodiment 1
The preparation of Graphite Powder 99 product
This embodiment has introduced with the inventive method and has prepared the Graphite Powder 99 product.Is surface-area 11.5m 2The Graphite Powder 99 sample 2.0g of/g is stirred in the 14g water.Add the solution of 0.11g phosphofluoric acid 4-chlorine diazobenzene in 7g water, emit a large amount of steam bubbles.Stir after 20 minutes, this product is filtered collection, carries out the Soxhlet extracted overnight and drying in baking oven with tetrahydrofuran (THF) (THF).Product analysis shows: contain 23ppm chlorine with the Graphite Powder 99 that is untreated and compare, it contains 597ppm chlorine.Therefore, the every square nanometers surface-area of this product contains 0.85 chloro-phenyl-.This product of ESCA (electron spectroscopy for chemical analysis) analysis revealed contains 1.4 atomic percent chlorine.On the surface of unreacted Graphite Powder 99, do not detect chlorine with ESCA.
Embodiment 2
The preparation of Graphite Powder 99 product
This embodiment has introduced with the inventive method and has prepared the Graphite Powder 99 product.The solution of 0.095g Tetrafluoroboric acid 4-nitro diazobenzene in 10g water is added in the stirred suspension of Graphite Powder 99 in 10g water of 2.0g embodiment 1.Stir after 15 minutes, this product in baking oven 125 ℃ down dry, carry out Soxhlet extracted overnight and dry with tetrahydrofuran (THF).Esca analysis shows: a N1s signal is arranged at the 406.1eV place, a signal is arranged at the 400.5eV place, relative area is 5.9: 1.This 406.1eV signal is by NO 2Base causes that the 400.5eV signal may be that azo group causes.There is not the signal of discovery corresponding to diazo 403eV place.The nitrogen content that merges is 4.0 atomic percents.On the unreacted Graphite Powder 99, do not detect nitrogen with ESCA.This shows that nitrophenyl links on the Graphite Powder 99 product.
Embodiment 3
The preparation of Graphite Powder 99 product
This embodiment has introduced with the inventive method and has prepared the Graphite Powder 99 product.Be prepared as follows right-NH 3C 6H 4N 2Cl 2Solution: 0.028g NaNO 2Cold soln in 3g water is added in the solution of the dense HCl of 0.16ml, 0.043g p-phenylenediamine and 5g water (stirring in ice bath).This cold diazonium thing solution is added in the suspension of the Graphite Powder 99 of 2.0g embodiment 1 and the water that 18g at room temperature stirs.Stir after 1 hour, this product is dry under 125 ℃ in baking oven, carries out Soxhlet extracted overnight and drying with THF.The esca analysis of this product shows that the concentration of nitrogen is 4.6 atomic percents.On unreacted Graphite Powder 99, do not detect any nitrogen by ESCA.This shows that aminophenyl links on this Graphite Powder 99 product.
Embodiment 4
The preparation of graphite fibre product
This embodiment introduction prepares the graphite fibre product with the inventive method.165 ℃ of following desiccated surfaces amass and are 0.43m in nitrogen atmosphere 2/ g, diameter are 8 microns graphite fibre two hours.This fiber was placed in the nitronium tetrafluoroborate basic weight pyridine solution in the anhydrous benzonitrile of 0.1M 2 minutes.This fiber is taken out,, carry out the Soxhlet extracted overnight with THF with anhydrous benzonitrile rinsing twice, and dry in baking oven.Esca analysis shows: at the 406.5eV place N1s signal is arranged, at the 400.5eV place one signal is arranged, relative area is 4.1: 1.This 406.5eV signal is by NO 2Base causes that the 400.5eV signal is to be caused by nitrogen in the primary sample and azo group.Do not finding signal corresponding to diazo 403eV place.The nitrogen content that merges is 2.4 atomic percents.Use 0.01M nitronium tetrafluoroborate basic weight pyridine solution, use the esca analysis that makes sample with quadrat method to show the nitrogen that 0.9 atom percentage amounts is arranged.The esca analysis of unreacted fiber shows the nitrogen that 0.2 atom percentage amounts is arranged.This shows that these two kinds of fiber products have been connected with nitrophenyl.
Embodiment 5
The preparation of carbon fiber product
This embodiment has introduced with the inventive method and has prepared the graphite fibre product.The solution of 0.095g Tetrafluoroboric acid 4-nitro diazobenzene in 10g water is added in the stirred suspension of graphite fibre in 100g water of 2.0g embodiment 4.Stir after 15 minutes, this fiber is taken out from this solution, dry under 125 ℃ in baking oven, carry out Soxhlet extracted overnight and dry with tetrahydrofuran (THF).Esca analysis shows: a N1s signal is arranged at the 406.7eV place, a signal, about 1: 1 of relative area are arranged at the 400.5eV place.This 406.7eV signal is by NO 2Base causes that the 400.5eV signal is to be caused by nitrogen in the primary sample and azo group.Do not find signal corresponding to diazo 403eV place.Be that 0.2 atomic percent is compared on the unreacted fiber, the nitrogen content of merging is 1.0 atomic percents.This shows that nitrophenyl links on the graphite fibre product.
Embodiment 6
The preparation of graphite fibre product
This embodiment has introduced with the inventive method and has prepared the graphite fibre product.Be prepared as follows right-NH 3C 6H 4N 2Cl 2Solution: 0.028gNaNO 2Cold soln in 3g water is added in the solution of the dense HCl of 0.16ml, 0.043g p-phenylenediamine and 5g water (stirring in ice bath).This cold diazonium thing solution is added in the suspension of the graphite fibre of 2.0g embodiment 4 and the water that 100g at room temperature stirs.Stir after 20 minutes, this product is taken out from solution, dry under 125 ℃ in baking oven, carry out Soxhlet extracted overnight and drying with THF.Esca analysis shows: compare with 0.2 atomic percent nitrogen is arranged on the unreacted fiber, the concentration of the nitrogen of this product is 1.7 atomic percents.This shows that aminophenyl links on this graphite fibre product.
Embodiment 7
The preparation of graphite fibre product
This embodiment introduction prepares the graphite fibre product with the inventive method.Be prepared as follows the solution of nitric acid 4-chloro-phenyl-diazonium thing: 0.014g NaNO 2Solution in 3g water is added in the stirred solution of 0.025g 4-chloroaniline, 0.070g 90% nitric acid and 3g water.Stir after 10 minutes, this diazonium thing solution is added in the stirring the mixture of the graphite fibre of 1g embodiment 4 and 50g water.Stir after 30 minutes, from this solution, take out this fiber, dry under 110 ℃ in baking oven this fiber, carry out Soxhlet extracted overnight, also dry with THF.Esca analysis shows that the concentration of the chlorine of this product is 0.4 atomic percent.On unreacted graphite fibre, do not detect chlorine by ESCA.This and bright chloro-phenyl-have been linked on this graphite fibre product.
Embodiment 8
The preparation of graphite fibre product
This embodiment has introduced with method of the present invention and has prepared the graphite fibre product.The graphite fibre of about 0.2g embodiment 4 is added in the stirred solution of 0.025g 4-chloroaniline, 0.07g 90% nitric acid and 70g water.Add 0.014gNaNO 2Solution in 2g water, and this mixture stirring 30 minutes.The on-the-spot nitric acid 4-chlorine diazobenzene that generates, this diazonium thing and graphite fibre react.From this solution, take out this fiber, dry under 110 ℃ in baking oven this fiber, carry out Soxhlet extracted overnight and drying with THF.The esca analysis of this product shows that the concentration of chlorine is 0.4 atomic percent.On unreacted graphite fibre, do not detect chlorine with ESCA.This shows that chloro-phenyl-linked on this graphite fibre product.
Embodiment 9
The preparation of carbon fabric product
This embodiment has introduced with method of the present invention and has prepared the carbon fabric product.Method with embodiment 1 is surface-area 5.3m 2The carbon fabric of/g and the reaction of phosphofluoric acid diazobenzene chloride.Carry out Soxhlet extracted overnight and this material sample of exsiccant with THF, use esca analysis, the chlorine that contains 0.03 atomic percent with the unreacted carbon fabric is compared, and this product contains the chlorine of 0.4 atomic percent.This shows that chloro-phenyl-links on this carbon fabric product.
Embodiment 10
The preparation of vitreous carbon product
This embodiment has introduced with method of the present invention and has prepared the vitreous carbon product.One small pieces glass carbon plate (about 0.5g) is stirred in the solution of 0.047g Tetrafluoroboric acid 4-nitro diazobenzene in 30g water 30 minutes.Take out this glass carbon plate, drying, carry out Soxhlet extracted overnight and drying with THF.Esca analysis shows: have the nitrogen of 0.6 atomic percent to compare with unreacted glass carbon plate, the concentration of the nitrogen of this product is 2.4 atomic percents.This shows that nitrophenyl links on this vitreous carbon product.
Embodiment 11
The preparation of activated carbon products
This embodiment introduces with method of the present invention and prepares activated carbon products.With the method for embodiment 1, allow the nitrogen BET surface-area be 762m 2/ g, pore-free surface amass and are 266m 2/ g, pore space are activated carbon and the reaction of phosphofluoric acid diazobenzene chloride of 0.20ml/g.Contain 0.02% chlorine with unreacted carbon and compare, carried out the Soxhlet extracted overnight with THF and this material sample of exsiccant contains 0.43% chlorine.Therefore, these activated carbon products contain the 0.12mmol/g chloro-phenyl-, or every square nanometers contains 0.09 chloro-phenyl-.This shows that chloro-phenyl-links on these activated carbon products.
Embodiment 12
The preparation of activated carbon products
This embodiment introduces and uses the inventive method to prepare activated carbon products.The solution of 1.66g Tetrafluoroboric acid 4-nitro diazobenzene in 100g water is added in the stirred suspension of the activated carbon of 7g embodiment 11 and 70g water.Emit steam bubble.Stir after 15 minutes, this mixture is dry under 125 ℃ in baking oven.This product carries out Soxhlet extracted overnight and dry with THF.Esca analysis shows at the 406.1eV place a N1s signal, and a signal is arranged at the 400.9eV place, and relative area is 3.2: 1.The signal at this 406.1eV place is by NO 2Base causes that the signal at 400.9eV place is to be caused by nitrogen in the initial sample and azo group.Have 0.3 atomic percent to compare with the unreacted activated carbon, the content of the nitrogen of merging is 5.6 atomic percents.This shows that nitrophenyl links on these activated carbon products.
Embodiment 13
The preparation activated carbon products
This embodiment has introduced with the inventive method and has prepared activated carbon products.Be prepared as follows right-NH 3C 6H 4N 2Cl 2: 0.483g NaNO 2Solution in 10g water is added in the solution of the water that the dense HCl of 2.87ml, 0.758g p-phenylenediamine and 30g stir in ice bath.This cold diazonium thing solution is added in the suspension in the activated carbon of 7.0g embodiment 11 and the water that 63g at room temperature stirs.Stir after 15 minutes, this product descended dry 1 hour at 125 ℃, carried out Soxhlet extracted overnight, also dry with THF.Esca analysis shows: compare with the nitrogen of 0.3 atomic percent of unreacted activated carbon, the concentration of the nitrogen of this product is 3.5 atomic percents.This shows that aminophenyl links on these activated carbon products.

Claims (14)

1. one kind prepares the method with carbon products of linking the organic group on the carbon material, and this method may further comprise the steps:
In the alpha proton reaction medium, at least a diazonium salt be selected from the reaction of following carbon material: Graphite Powder 99, graphite fibre, carbon fiber, carbon fabric, vitreous carbon product and activated carbon products;
Described diazonium salt has organic group.
2. the process of claim 1 wherein that this diazonium salt is from the primary amine on-site preparation.
3. the method for claim 2, wherein this diazonium salt is by primary amine, nitrite and acid-respons on-site preparation.
4. the method for claim 3, wherein this nitrite is the nitrous acid metal-salt, and uses the acid of monovalent.
5. the method for claim 2, wherein this diazonium salt is by this primary amine and nitrite reaction on-site preparation, and this primary amine contains a strong acid.
6. the method for claim 2, wherein this diazonium salt is by the reactant aqueous solution on-site preparation of this primary amine and nitrogen peroxide.
7. the method for claim 2, wherein this aprotic medium is an aqueous medium, and this primary amine is formula A yArNH 2Amine, wherein:
Ar is selected from following aryl: phenyl, naphthyl, anthryl, phenanthryl, xenyl and pyridyl;
A is a substituting group that is selected from the following aryl independently:
One is selected from following functional group: OR, COR, COOR, OCOR, COONa, COOK, COO -NR 4 +, halogen, CN, NR 2, S n, SO 3H, SO 3Na, SO 3K, SO 3 -NR 4 +, NR (COR), CONR 2, NO 2, PO 3H 2, PO 3HNa, PO 3Na 2, N=NR, N 2 +X -, NR 3 +X -And PR 3 +X -With
A linearity, branching or cyclic alkyl replaces or replaces with one or more said functional group;
R is hydrogen, C independently 1-20Alkyl or aryl;
N is the integer of 1-8;
X -It is halogen ion or from mineral acid or organic acid deutero-negatively charged ion; With
Y is following integer: being 1-5 when Ar is phenyl, is 1-7 when Ar is naphthyl, is 1-9 when Ar is anthryl, phenanthryl or xenyl, or is 1-4 when Ar is pyridyl.
8. the process of claim 1 wherein that this diazonium salt is an on-site preparation.
9. the process of claim 1 wherein that this diazonium salt is to prepare from primary amine in advance.
10. the process of claim 1 wherein that this alpha proton reaction medium is an aqueous medium.
11. the process of claim 1 wherein that the organic radical of this diazonium salt is replacement or unsubstituted, and be selected from aliphatic group, ring-type organic radical or have the organic compound of aliphatic series part and circular part.
12. the process of claim 1 wherein that this alpha proton reaction medium is a water.
13. the process of claim 1 wherein that this alpha proton reaction medium is based on the medium of alcohol.
14. carbon products according to the method preparation of claim 1.
CNB011046538A 1994-12-15 1995-12-14 Process for preparing carbon products having organic group linked to carbon material Expired - Lifetime CN100360619C (en)

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